(S)-(+)-2-(-amino)-1-phenylethanol | 14467-53-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-(+)-2-(-amino)-1-phenylethanol
• 英文别名: (S)-2-(isopropylamino)-1-phenylethanol；(S)-2-(2-propylamino)-1-phenylethanol；(1S)-1-phenyl-2-(propan-2-ylamino)ethanol
• CAS: 14467-53-9
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: YANYGOBZUASRHR-LLVKDONJSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  272.7±7.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-(+)-扁桃酸 在 lithium aluminium tetrahydride 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 copper dichloride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.5h， 生成 (S)-(+)-2-(-amino)-1-phenylethanol
  参考文献：
  名称：

  Synthesis of chiral non-racemic 1,2-diamines from O-acetyl mandelic acid: application in enantioselective deprotonation of epoxides and diethylzinc addition to aldehydes

  摘要：

  A variety of 1,2-diamines were synthesized from readily available O-acetyl mandelic acid. These diamines were used in the synthesis of key intermediates for the preparation of (-)-utenone A and carbovir involving enantioselective deprotonation of epoxides, The addition of Et2Zn catalysed by some of these diamines was also studied and although ees were not high, some interesting observations were made in the outcome of the stereochemistry of the product. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)00376-9

文献信息

• [EN] ISOXAZOLINES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE<br/>[FR] ISOXAZOLINES EN TANT QU'INHIBITEURS DE L'HYDROLASE DES AMIDES D'ACIDES GRAS
  申请人：INFINITY PHARMACEUTICALS INC

  公开号：WO2010135360A1

  公开（公告）日：2010-11-25

  The present invention provides isoxazoline FAAH inhibitors of the formula (I): or pharmaceutically acceptable forms thereof, wherein each of G, Ra, Rb, Rc, and Rd are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable form thereof, and a pharmaceutically acceptable excipient. The present invention also provides methods for treating an FAAH-mediated condition comprising administering a therapeutically effective amount of a compound of formula (I), or pharmaceutically acceptable form thereof, to a subject in need thereof.

  本发明提供了式(I)的异噁唑啉FAAH抑制剂或其药用可接受形式，其中G、Ra、Rb、Rc和Rd中的每一个如本文所定义。本发明还提供了包括式(I)化合物或其药用可接受形式以及药用可接受赋形剂的药物组合物。本发明还提供了治疗FAAH介导疾病的方法，包括向需要的受试者施用式(I)化合物或其药用可接受形式的治疗有效量。
• The Direct Catalytic Asymmetricα-Aminooxylation Reaction: Development of Stereoselective Routes to 1,2-Diols and 1,2-Amino Alcohols and Density Functional Calculations
  作者：Armando Córdova、Henrik Sundén、Anders Bøgevig、Mikael Johansson、Fahmi Himo

  DOI：10.1002/chem.200400137

  日期：2004.8.6

  for the asymmetric alpha-oxidation reaction and found that several proline derivatives were also able to catalyze the transformation with excellent enantioselectivities. Moreover, stereoselective routes for the synthesis of monoprotected vicinal diols and hydroxyketones were found. In addition, short routes for the direct preparation of enantiomerically pure epoxides and 1,2-amino alcohols are presented

  描述了脯氨酸催化的酮和醛的直接不对称α-氨基氧基化。未修饰的酮或醛与亚硝基苯之间的脯氨酸催化反应具有出色的非对映选择性和对映选择性。在所有测试的情况下，分离出的相应产品的ee均> 95％。甲基烷基酮在亚甲基碳原子上被区域特异性氧化，得到对映体纯的α-氨基氧基化酮。另外，环状酮可以以非常高的选择性被α，α'-二氧化，为相应的二氨基氧基化的酮提供大于99％的ee。研究了脯氨酸催化的不对称α-氨氧基化反应的反应机理，为了进一步研究可能的过渡态的性质，我们进行了密度泛函理论（DFT）计算。我们还针对不对称α-氧化反应筛选了其他有机催化剂，发现几种脯氨酸衍生物也能够以出色的对映选择性催化转化。此外，发现了用于合成单保护的邻位二醇和羟基酮的立体选择路线。另外，提出了直接制备对映体纯的环氧化物和1,2-氨基醇的捷径。直接催化的α-氧化也是立体选择性制备β-肾上腺素受体拮抗剂的新途径。我们还针对不对称的α
• THYROID RECEPTOR LIGANDS
  申请人：Ryono Denis E.

  公开号：US20100298276A1

  公开（公告）日：2010-11-25

  Thyroid receptor ligands are provided which have the general formula I wherein: R 1 is R 2 and R 3 are the same or different and are hydrogen, halogen, alkyl of 1 to 4 carbons or cycloalkyl of 3 to 5 carbons, provided that at least one of R 2 and R 3 is other than hydrogen; R 4 is R 5 and R 6 are the same or different and are selected from hydrogen, aryl, heteroaryl, alkyl, cycloalkyl, aralkyl or heteroaralkyl. R 7 is aryl, heteroaryl, alkyl, aralkyl, or heteroaralkyl; R 8 is aryl, heteroaryl, or cycloalkyl; R 9 is R 7 or hydrogen; R 10 is hydrogen, halogen, cyano or alkyl; R 11 and R 12 are each independently selected from the group consisting of hydrogen, halogen, alkoxy, hydroxy (—OH) cyano, and alkyl; R 13 is carboxylic acid (COOH) or esters thereof, phosphonic and phosphinic acid or esters thereof, sulfonic acid, tetrazole, hydroxamic acid, thiazolidinedione, acylsulfonamide, or other carboxylic acid surrogates known in the art; R 14 and R 15 may be the same or different and are selected from hydrogen and alkyl, or R 14 and R 15 may be joined together forming a chain of 2 to 5 methylene groups [—(CH2)m-, m=2, 3, 4 or 5], thus forming 3- to 6-membered cycloalkyl rings; R 16 is hydrogen or alkyl of 1 to 4 carbons; R 17 and R 18 are the same or different and selected from hydrogen, halogen and alkyl; n is 0 or an integer from 1 to 4; X is oxygen (—O—), sulfur (—S—), sulfonyl (—SO 2 —), sulfenyl (—SO—) selenium (—Se—), carbonyl (—CO—), amino (—NH—) or methylene (—CH2-); wherein the substituents are as described herein. In addition, a method is provided for preventing, inhibiting or treating diseases or disorders associated with metabolism dysfunction or which are dependent upon the expression of a T 3 regulated gene, wherein a compound as described above is administered in a therapeutically effective amount.

  提供了甲状腺受体配体，其具有一般公式I，其中：R1为R2和R3，R2和R3相同或不同，为氢、卤素、1至4个碳原子的烷基或3至5个碳原子的环烷基，但至少其中一个为非氢；R4为R5和R6，R5和R6相同或不同，选择自氢、芳基、杂环芳基、烷基、环烷基、芳基烷基或杂环芳基；R7为芳基、杂环芳基、烷基、芳基烷基或杂环芳基；R8为芳基、杂环芳基或环烷基；R9为R7或氢；R10为氢、卤素、氰基或烷基；R11和R12各自独立选择自氢、卤素、烷氧基、羟基（—OH）、氰基和烷基；R13为羧酸（COOH）或其酯、膦酸和膦酸酯、磺酸、四唑、羟胺酸、噻唑二酮、酰基磺胺或艺术中已知的其他羧酸替代物；R14和R15可相同或不同，选择自氢和烷基，或R14和R15可结合形成2至5个亚甲基组成的链[—(CH2)m-，m=2、3、4或5]，从而形成3至6成员的环烷基环；R16为氢或1至4个碳原子的烷基；R17和R18相同或不同，选择自氢、卤素和烷基；n为0或1至4的整数；X为氧（—O—）、硫（—S—）、砜基（—SO2—）、砜基（—SO—）、硒（—Se—）、羰基（—CO—）、氨基（—NH—）或亚甲基（—CH2-）；其中取代基如上述所述。此外，提供了一种方法，用于预防、抑制或治疗与代谢功能障碍或依赖于T3调节基因表达的疾病或障碍，其中上述化合物以治疗有效剂量给予。
• Asymmetric syntheses with a new optically active perhydronaphthalene based chiral auxiliary
  作者：David P.G. Hamon、Jeffrey W. Holman、Ralph A. Massy-Westropp

  DOI：10.1016/s0040-4020(01)80228-3

  日期：——

  (1R,4aS,8S,8aS)-8-(5′-Methoxy-2′-methylphenyl)-8-methyldecahydro-1-naphthalenol 3a is a highly efficient chiral auxiliary in the Diels-Alder addition of its acrylate ester 5 and in the DIBAL-H and Grignard reactions of its phenylglyoxylate ester 7.

  （1 R，4a S，8 S，8a S）-8-（5'-甲氧基-2'-甲基苯基）-8-甲基十氢-1-萘3a是Diels-Alder添加的高效手性助剂丙烯酸酯5以及在DIBAL-H和Grignard反应中的苯乙醛酸酯7。
• ISOXAZOLINES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE
  申请人：Behnke Mark L.

  公开号：US20110028478A1

  公开（公告）日：2011-02-03

  The present invention provides isoxazoline FAAH inhibitors of the formula (I): or pharmaceutically acceptable forms thereof, wherein each of G, R a , R b , R c , and R d are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable form thereof, and a pharmaceutically acceptable excipient. The present invention also provides methods for treating an FAAH-mediated condition comprising administering a therapeutically effective amount of a compound of formula (I), or pharmaceutically acceptable form thereof, to a subject in need thereof.

  本发明提供了式(I)的异噁唑烷FAAH抑制剂或其药学上可接受的形式，其中G、Ra、Rb、Rc和Rd的定义如本文所述。本发明还提供了包括式(I)化合物或其药学上可接受的形式和药学上可接受的赋形剂的制药组合物。本发明还提供了治疗FAAH介导的疾病的方法，包括向需要治疗的患者施用式(I)化合物或其药学上可接受的形式的治疗有效量。